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Sulfonated polyphosphazenes, uses thereof, and methods for preparing same

a technology of sulfonated polyphosphazene and polydichlorophosphazene, which is applied in the field of sulfonated polyphosphazene, uses of sulfonated polyphosphazene, and methods for preparing the same. it can solve the problems of significant decrease in the yield and molecular weight of the final polymer product, polydichlorophosphazene with sodium salts of sul

Inactive Publication Date: 2007-01-30
INNOVO BIOPOLYMERS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This method ensures precise control over sulfonation, enabling the production of polymers with desired properties, including high molecular weights and thermal stability, suitable for applications like proton conducting membranes in fuel cells, with improved hydrophobic-hydrophilic balance and chemical stability.

Problems solved by technology

Degradation and crosslinking can significantly decrease the yield and molecular weight of the final polymer product.
And, reacting polydichlorophosphazene with sodium salts of sulfonic acids under the reaction conditions described herein did indeed fail to produce useful polymeric product.

Method used

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  • Sulfonated polyphosphazenes, uses thereof, and methods for preparing same
  • Sulfonated polyphosphazenes, uses thereof, and methods for preparing same
  • Sulfonated polyphosphazenes, uses thereof, and methods for preparing same

Examples

Experimental program
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example 2

[0039]4-hydroxybenzenesulfonic acid, sodium salt dehydrate (4.57 g, 19.7 mmole) is dissolved in water (100 mL) and is titrated with a NaOH solution (19.7 ml, 1 N). The resultant 4-hydroxybenzenesulfonic acid, disodium salt is lyophilized.

[0040]4-hydroxybenzenesulfonic acid, disodium salt (0.50 g, 2.12 mmol)) benzyltriethylammonium bromide (0.58 g, 2.12 mmol), sodium phenoxide (3.61 ml of a 12.3% w / v solution in diglyme, 3.94 mmol), chlorobenzene (40 mL), and DMF (4 ml) are placed in a 100 CC Telfon™ reaction tube fitted with a magnetic stir bar. Under a stream of nitrogen the reaction mixture is heated to 105° C. and agitated for 30 minutes after which time, a solution of polydichlorophosphazene in diglyme (2.00 mL of a 9.6% solution w / v, 0.83 mmole) is added. The reaction mixture is heated at 120° C. and agitated for two hours. The resultant polymer is precipitated with hexane and dried under vacuum. The yield was 0.47 g. The polymer was characterized by gel permeation chromatograp...

example 3

[0041]4-hydroxybenzenesulfonic acid, sodium salt dehydrate (4.57 g, 19.7 mmole) is dissolved in water (100 mL) and is titrated with a NaOH solution (˜19.7 mL, 1 N). The resultant 4-hydroxybenzenesulfonic acid, disodium salt is lyophilized.

[0042]4-hydroxybenzenesulfonic acid, disodium salt (0.36 g, 1.52 mmol)) benzyltriethylammonium bromide (0.41 g, 1.52 mmol), sodium phenoxide (4.55 ml of a 12.3% w / v solution in diglyme, 4.16 mmol), chlorobenzene (40 mL), and DMF (4 ml) are placed in a 100 CC Telfon™ reaction tube fitted with a magnetic stir bar. Under a stream of nitrogen the reaction mixture is heated to 105° C. and agitated for 30 minutes after which time, a solution of polydichlorophosphazene in diglyme (2.00 mL of a 9.6% solution w / v, 0.83 mmole) is added. The reaction mixture is heated at 120° C. and agitated for two hours. The resultant polymer is precipitated with hexane and dried under vacuum. The yield was 0.42 g. The polymer was characterized by gel permeation chromatogra...

example 4

[0043]4-hydroxybenzenesulfonic acid, sodium salt dehydrate (4.57 g, 19.7 mmole) is dissolved in water (100 mL) and is titrated with a NaOH solution (˜19.7 mL, 1 N). Benzyltriethylammonium bromide (5.36 g, 19.7 mmole) is added to this mixture and the resultant product is lyophilized, yielding a white powder of 4-hydroxybenzenesulfonic acid, dibenzyltriethylammonium.

[0044]4-hydroxybenzenesulfonic acid, dibenzyltriethylammonium (5.73 g, 8.45 mmol), diglyme (40 mL), and DMF (5 mL) are placed in a 100 CC Teflon™ reaction tube fitted with a magnetic stir bar. Under a stream of nitrogen the reaction mixture is heated to 120° C. and agitated for two hours after which time, a solution of polydichlorophosphazene in diglyme (0.33 mL of a 15% solution w / v, 0.4 mmole) is added. The resultant heterogeneous mixture is heated at 120° C. and agitated for two hours. The solution is cooled to 80° C. and the organic layer is removed. The precipitate is dissolved in water and purified by dialysis agains...

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Abstract

Polyphosphazene polymers having at least one sulfonated pendent group, and no more than five different sulfonated pendent groups, repeated along the polymer chain, wherein at least one the repeated sulfonated pendent groups links at least one SO3− group to the polymer chain through a nitrogen-free linkage containing at least three carbon atoms, are disclosed, along with methods of making same, and uses therefor.

Description

[0001]This application claims the priority of U.S. Provisional Application Ser. No. 60 / 384,981, filed on Jun. 3, 2002, the disclosures of which are hereby incorporated by reference in their entireties.[0002]This invention relates to sulfonated polyphosphazenes, uses of sulfonated polyphosphazenes, and methods for preparing sulfonated polyphosphazenes. More specifically it relates to polyphosphazenes that contain pendent groups that are SO3− substituted, the uses of such polyphosphazenes, and their methods of preparation.[0003]Polyphosphazenes comprise a broad class of macromolecules having a (—N═P—) polymer backbone based on the repeating unit (NPR2)n. Within this backbone the nitrogen and phosphorus atoms are separated by alternating single and double bonds. Through selective functionalization this backbone can be substituted to yield polymers having manifold characteristics. Substituted polyphosphazenes have myriad applications and utilities that depend upon the nature of their pe...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): H01M8/10C08G79/02C08L85/02H01B1/06H01M6/18H01M8/02H01M10/05
CPCC08G79/025C08L85/02Y02E60/523C08G2650/02Y02E60/50
Inventor ANDRIANOV, ALEXANDERCHEN, JIANGPINGSARGENT, JONATHANMARIN, ALEXANDER
Owner INNOVO BIOPOLYMERS LLC
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